Carolyn Childers and Lindsay Kaplan like to say they met at a networking event in early 2017—a bad one. “We rolled our eyes at each other,” says Kaplan, of the stiff sit-down dinner at a Manhattan restaurant. Two years later, the pair officially founded what they consider an alternative: Chief, an exclusive, $5,800-per-year and up networking club for female executives, now worth more than $1 billion. “I always joke that if a bad networking event can bring together two co-founders to build something new, just imagine what could happen if you really build an intentional one,” says Childers, Chief’s CEO.
If Chief is any guide, what such a network can do—first and foremost—is explode in size. By October 2022, it had hit 20,000 members, adding them at a pace of roughly 900 per month. The club now has a much-vaunted waiting list of 60,000 women who are eager to add Chief’s mission statement to their LinkedIn bios: “to drive more women to the top—and keep them there.”
The same year Childers sat down at that restaurant in Manhattan, she left her position as an executive at household services startup Handy to become entrepreneur-in-residence at Primary Venture Partners. In brainstorming sessions with Ben Sun, a tech VC and Primary’s co-founder, Childers had been inspired by clubs including the Young Presidents’ Organization—a discreet nonprofit for young CEOs—and decided to build off of YPO’s model of exclusivity and group coaching. But her startup would be different in two ways: It would be for high-ranking women executives—vice presidents and up—and it would aim to make money. In late 2017, Childers approached Kaplan, then a vice president at Casper, a VC-backed mattress company, where she was behind such marketing initiatives as an insomnia chatbot and a sleep-themed magazine called Woolly. Kaplan eventually joined Childers’ venture as chief brand officer and co-founder.
Chief’s stratospheric rise was far from certain. When the company launched in February 2019 out of a warmly lit “clubhouse” in New York’s Tribeca area, it was quickly compared to The Wing. That buzzy women’s coworking business, launched three years earlier, cast a long shadow from its own clubhouse nearby.
Yet the aftermath of the pandemic officially killed The Wing, already weakened by allegations it mistreated employees of color and flogged a brand of shallow, Instagram-friendly feminism—and little else. (Founder Audrey Gelman had vowed to do better, but ultimately resigned in 2020.)
Chief, meanwhile, thrived—so much so, in fact, that some members are wondering whether a private club that promised exclusivity and individually tailored coaching has grown too fast.
Comparably light on real estate—it has five clubhouses—Chief switched its operations to digital during the pandemic, expanded to new cities, and watched membership climb. In March 2022, the company, then over 12,000 members strong, raised $100 million in a Series B round led by Alphabet’s VC fund, CapitalG. The series brought its total backing to $140 million and pushed it into the ranks of the unicorns, with a valuation of $1.1 billion.
With annual membership dues of up to $8,900, revenue could now be as high as $130 million per year, based on average membership fees. (Chief declined to provide revenue figures.) In January, the company said it had signed corporate deals with giants like Morgan Stanley and IBM to provide bulk memberships for their senior female executives. (Chief says companies already sponsor around 70% of their members.) In February, the company opened its first international clubhouse, in London.
Chief is now bigger by membership—and likely far more lucrative—than The Wing ever was.
Fueling that growth, at least in part, is what fans and critics alike agree is Chief’s powerful observation: that senior women in corporate America are stressed out, and often lonely. That was the case before the pandemic, but COVID’s erosion of support systems, from childcare to industry networks to a night out with friends, left professional women even more desperate to find peers who understand the demands of their jobs, members interviewed for this story say.
Current and former members who spoke to Fortune say they were surprised by how well Chief’s pitch landed—and just how little competition its mix of coaching and support had among the reams of women’s networking groups. (Fortune offers its own membership groups for executives, including one for women.)
Several members pointed to remarkable shifts in their careers during their time with Chief, largely due to their close friendships with other members. They bounced back from a layoff, successfully asked for a raise, or, in the case of New York City member Sandhya Jain-Patel, finally landed her dream job as a manager of diversity and inclusion at Lucasfilm—a jump she says her fellow Chief members coached her through.
But interviews with 15 current and former members suggest that some among Chief’s customer base are struggling to see its value beyond the initial introductions it makes. Many of them say that membership turnover is high and the relationship between some of Chief’s most engaged members and its leadership is fraying. (Chief disputes these claims.) As Chief continues to grow, the question now is whether scaling up aligns with the company’s initial purpose: to build a business founded on exclusivity, and to give members the connections and guidance they had been struggling to find elsewhere.
Chief’s ‘Core’ meetings and clubhouses
Chief’s London clubhouse smells like fresh paint. It’s just a couple hours before the launch party for the company’s latest outpost, a five-story Georgian townhouse tucked in a leafy Bloomsbury square. Its cozy English period fixtures are interspersed with jewel-toned sofas, bright modern art, and stacks of color-coordinated books by the likes of Sheila Heti and Annie Leibovitz. There is a conspicuous lack of pink, the Wing’s signature color.
The Wing made money as a real estate business, renting women flexible coworking spaces with chic bathrooms; evening events and networking opportunities were thrown in.
By contrast, Chief offers members services including group leadership coaching, meet-ups and member forums, and events and Q&As with speakers like Michelle Obama, Shonda Rhimes, Amy Poehler, and Amal Clooney. Sometimes events take place at Chief’s clubhouses in New York, San Francisco, Los Angeles, Chicago and London, but it has also held on to a pandemic-era policy: Its “Core” meetings are held virtually, often combining members from different cities.
Women who aren’t signed up by their company are either approached by Chief to join—usually via LinkedIn, the only social network the company uses—or apply on their own, often via references from other members.
The cost of a membership is based on seniority—$5,800 per year for VP-level members, and $7,900 for C-suite members (the prices are £5,800 and £7,900 for U.K. members). And while access to clubhouses used to be included, last year it became a $1,000 add-on for new members. Childers and Kaplan say 15% to 20% of members receive grants of varying sizes, and its 20,000 members are split nearly evenly between the VP and C-Suite levels.
Membership, like corporate America at large, skews white. The company says 32% of its members are women of color.
Chief’s 60,000-person waiting list, meanwhile, is mostly made up of applicants in places where the company hasn't opened yet, as well as those who are too junior to join, the co-founders say. Men are technically allowed to join, even if there aren’t any among the ranks yet.
Despite the glitzy clubhouse events, Chief’s co-founders say its tentpole offering is really its Core groups—cohorts of eight to 12 women who meet for two hours once a month, moderated by an executive coach. Some Core meetings follow a structured coaching curriculum; others are more of a once-a-month catch-up on the members’ work and personal lives, members told Fortune.
In 2022, the company started using an algorithm to match women into Core groups, factoring in industry and job title and ensuring no individual woman was the “only” in her group—the only woman of color, or the only woman who is married or has children. A human manually reviews each group before it’s launched, the company says.
That technology component and the focus on corporate membership deals appealed to Laela Sturdy, the now-head of CapitalG, who led Chief’s Series B round and sits on Chief’s board. She also recognized the size of Chief’s potential market: Chief says that 6 million women are at VP-level and above in the U.S. and U.K. combined, based on analysis commissioned from LinkedIn.
“What is amazing about this business model is it’s very similar to product-led growth software companies, of which I’ve invested in quite a few,” says Sturdy.
But current and former members interviewed by Fortune have cited glitches in Chief’s business model. Some complain that Chief’s main offering—its Core groups—are hit or miss, while others charge that the network isn’t living up to its mission to change the face of corporate leadership.
Chief’s ‘growing pains’
On March 8—International Women’s Day—Denise Conroy, founder of professional coaching business Themy and a founding Boston member, announced on LinkedIn she was quitting Chief.
“I’m quitting because I had bigger hopes for this organization. Bringing 20k accomplished women together has the potential to change the world. Yet, mobilization doesn't seem to be on the agenda,” she wrote.
The organization “seems to have chosen the performative over the meaningful,” she argued, saying that there had been no appetite to take a stand on Roe v. Wade, and that three women of color she had referred for membership had all been “ghosted.”
Conroy told Fortune that she’d complained to Chief leadership privately for months; she acknowledged in a separate LinkedIn post that Chief had reprimanded her for self-promotion on the platform last fall.
“Pay attention: this is white feminism at its core,” Conroy wrote in the March 8 post. She stated in a follow-up post that Chief had ended her membership and she’d received a refund for the quarter. As of Thursday, her initial post had been liked more that 5,000 times and had been shared over 200 times.
In a letter signed by Childers and Kaplan, Chief responded publicly that intersectional feminism has “informed every facet of who we are,” pointing to its many members of color, its internal programming on diversity, and donations to women’s rights organizations. (Fortune spoke to seven members of color for this story; all said they never felt discriminated against.) The organization also said it donated $250,000 to organizations fighting to protect reproductive rights and held events on reproductive rights with the ACLU and Planned Parenthood.
The company said in a statement to Fortune that it was rolling out a series of “listening tours” this week, but argued that Conroy’s post had led to “significant misinformation” being spread about the business.
“Thousands of members support us and sent us emails saying so, they just have no interest in inserting themselves in a public social media forum,” a spokesperson for the company said.
For some of the current and former members Fortune spoke to, the post and the response to it represented a public explosion of long-simmering discontent within the private club. While some are frustrated that Chief isn’t living up to its ideals, the most common complaint among the 15 current and former Chief members Fortune interviewed is that as Chief has grown rapidly, operations haven’t seemed to catch up. The Core experience—always spotty—has become patchier, they say; emails have gone unanswered, and customer service has dropped. The “ghosting” Conroy complained of is now widespread, say several members interviewed for this story.
Jessica Clifton, a former member in Los Angeles and head of brand and marketing advisory at Media.Monks, said that while she considers Chief a brilliant concept, it took almost four months for the company to match her with a Core group after she joined in March 2021. When she asked for a transfer, she was put in one that felt pieced together from the remnants of past groups, she says.
“It wasn’t the best fit, either,” she adds. “Ultimately, most people I knew in Chief two years ago have canceled their memberships due to lack of value.”
In the past, a member unhappy with her Core group could easily ask to be reassigned. But several members say they now email a generic inbox that is slow to respond—if it responds at all.
“Like all companies, we have our ‘growing pains.’ Our biggest has been with Core Group transitions, but we are proud of how we’ve iterated and fixed that process,” Chief said in a statement to Fortune in response to the criticism.
The company also said that while response times for members looking to switch groups were “arduous and inexcusably long” a few months ago, they have fixed this problem; it now takes less than a week on average to change groups, the company says.
Some current and former members Fortune spoke to echo Chief’s own argument that the company—now four years old—is trying to nail what’s admittedly a lofty objective: create real and lasting chemistry between strangers, at scale.
And members’ frustration isn’t universal. Dolores Estrada, chief operating officer at PEAK Grantmaking and a former member in D.C., said her Core group gelled immediately.
“I really walked away with such a great experience,” she said. Still, she declined to renew, because she felt Chief had served its purpose.
“I got everything I needed to figure out how to better maneuver the next portion of my life,” she said.
Members interviewed for this story who are satisfied with Chief say some of their peers expect Chief to provide a ready-made network, but that’s not the case.
“Chief is not a done-for-you experience (and I don’t know any community that is),” says Osnat Benari, a product management consultant and a New York member. “But just like in life, if you don’t show up you can’t control your experience.”
But even members Fortune spoke to with positive experiences claim the patchiness of the Core groups is exacerbating the company’s turnover. In April last year, Chief instituted a policy that bars members from missing more than two Core sessions per year without explanation, or else be kicked out of the group. Members say the approach backfired, coming across as patronizing and failing to recognize the demands on senior women’s time. Chief says the policy was instituted at members’ request.
Multiple current and former members interviewed for this story estimate that Chief is losing up to 50% of its members every year, based on the non-renewal rate in their own Core groups.
Chief said the turnover estimate of 50% is false and misleading, and that churn in the Core groups wasn’t representative of retention. The company declined to share its renewal rate.
Dedicated to each other, but maybe not to Chief
As Chief has grown, so too have the complaints of some of the network’s most engaged members who run popular off-shoot groups. There are groups for members focused on career transitions or joining a board, and there are groups specifically for Black and South Asian members.
Late last year, Eugina Jordan, chief marketing officer at the Telecom Infra Project and then a member in Boston, read a Chief blog post about corporate women suffering from burnout, and decided to take the article’s advice on when to step back. She quit Chief.
Jordan, who calls Chief a career-transforming experience, said she was spending six to seven hours a week organizing and moderating groups and meet-ups, from a Boston-themed group to events bringing in LinkedIn experts and career coaches. Something had to give, she says—plus, she had already converted her Chief network into what she calls her “board of advisors,” only ever a text or a lunch date away.
“I wanted the community. I wanted to belong. I wanted a support group—and that’s what I got,” she says.
Groups like Jordan’s are started, administered and led almost exclusively by members themselves, multiple women who spoke to Fortune say. While starting and running the groups is entirely voluntary, one former member characterized the “free labor” dynamic as ironic given Chief’s membership fees.
“We want to be clear that we never expect our members to spearhead niche groups or host get-togethers—we launched the meet-ups tool to make it easier for them to gather within the community, if they choose to,” the company told Fortune. Chief also says it’s actively hiring community managers to help organize programming in major metro areas and to support members’ own events.
The popular off-shoot groups also showcase a recurring dynamic of Chief: members say they are deeply loyal to each other, but less devoted to the business itself. That sentiment raises questions about how Chief can retain members once they—like Jordan—have recreated their Chief support group on WhatsApp.
Chief says its influence makes a difference. Citing a March 2022 member survey, Kaplan says 80% of members feel more confident and supported in their roles since joining Chief, and 50% of members have received a promotion or a raise while belonging to Chief.
The frustration among some members who spoke to Fortune raises questions not just about the operational strains of growing a VC-backed startup, but about the inherent tensions of building a business based around women’s identities—and ultimately, their marginalization in the workplace.
One former member suggested that tension could grow as Chief shifts towards more stable corporate contracts. Blue-chip companies may see Chief as a relative bargain compared to other womens’ networks and support—and as a way to tick a “supporting women” box without risking real change. The things that matter most for women’s careers—pay raises, promotions, stock options, job security, good parental leave and other protections—cost money; most of them much more than $5,800 and up.
Some members interviewed for this story also worry that serving more corporate clients will leave the network with less incentive to take a stand on political issues and less of a stake in helping individual members negotiate raises or find new jobs. It’s a worry that Chief says is unfounded since most members were already sponsored by their companies.
“The hurdle we saw was women being comfortable asking for that sponsorship,” the company said in a statement to Fortune. “This isn’t about allowing companies to ‘box check.’ It’s about making it easier for women who want to be part of Chief to get the support they deserve.”
The next stage of Chief
Childers and Kaplan, sitting in the brand-new sitting room on an upper floor of the London clubhouse, say they aren’t worried about the economic downturn hitting their bottom line. They say the corporate contracts they announced in January prove companies understand the need to retain and support senior women regardless of market fluctuations.
The pair say they’re not considering another fundraising round right now. “We don’t need to raise capital,” Childers says. They also say they feel no pressure from investors to scale beyond Chief’s current size. “We have the right investors who understand that the mission comes first,” says Childers. “And that if you're not true to that mission, short term scaling doesn't mean anything.”
Ken Chenault, chairman and managing director at General Catalyst and the former CEO of American Express, who invested in both of Chief’s fundraising rounds, acknowledged the “tension” between scaling up and exclusivity. But he’s convinced Chief can maintain its “specialness” even as it grows.
“I think they’ll continue to work on curating member experiences,” he said.
That’s ultimately what current members—and even some former ones—want for the startup. Getting female executives from different industries into the same room—a rarity in business—was often enough to power Chief’s early years. Now that Chief has assembled tens of thousands of women, the question is whether it can fine tune its matchmaking and develop programming that satisfies more members, justifies its dues, and fulfills the promise of its tagline.
